Cesium carbonate → HCID 71080417, compound

HRID 576578Notes

Reaction equation

Br[C:2]1[CH:3]=[CH:4][C:5]([C:8]([F:11])([F:10])[F:9])=[N:6][CH:7]=1.[Br:12][C:13]1[CH:14]=[C:15]2[C:19](=[CH:20][CH:21]=1)[NH:18][CH:17]=[CH:16]2.C(=O)([O-])[O-].[Cs+].[Cs+]>CN(C=O)C>[Br:12][C:13]1[CH:14]=[C:15]2[C:19](=[CH:20][CH:21]=1)[N:18]([C:2]1[CH:7]=[N:6][C:5]([C:8]([F:11])([F:10])[F:9])=[CH:4][CH:3]=1)[CH:17]=[CH:16]2

Participants

Conditions

Temperature: 90 °C

Procedure

5-Bromo-2-(trifluoromethyl)pyridine (2.075 g, 9.18 mmol) was added to a solution of 5-bromo-1H-indole (1.5 g, 7.65 mmol) and in DMF (20 mL) followed by cesium carbonate (7.48 g, 22.95 mmol), and the mixture was stirred at 90° C. for 15 min. Insoluble solids were filtered, filtrate was concentrated and partitioned between ethyl acetate and water. Organic layer was separated, washed with brine, dried over sodium sulphate and filtered. The filtrate was concentrated in vacuo and purified by flash chromatography using 5% ethyl acetate in pet ether to afford title compound (1.1 g, 42.1%) as an off-white solid. 1H NMR (300 MHz, DMSO-d6): δ 9.09 (d, J=2.4 Hz, 1H), 8.37 (dd, J1=2.4 Hz, J2=8.4 Hz, 1H), 8.11 (d, J=8.4 Hz, 1H), 7.91 (m, 2H), 7.68 (d, J=9.0 Hz, 1H), 7.37 (dd, J1=1.8 Hz, J2=8.4 Hz, 1H), 6.82 (d, J=3.0 Hz, 1H).

Workup

filtrationInsoluble solids were filtered
concentrationfiltrate was concentrated
custompartitioned between ethyl acetate and water
customOrganic layer was separated
washwashed with brine
dry with materialdried over sodium sulphate
filtrationfiltered
concentrationThe filtrate was concentrated in vacuo
custompurified by flash chromatography

Sources & evidence

ORD record: ord-b7dc6fe1d090455ba9889b878b2d5f40
Source dataset: uspto-grants-2015_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09040517B2

Reaction notes

Loading…